Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates

Viktor A. Dmitriev, Mariia M. Efremova, Alexander S. Novikov, Vladimir V. Zarubaev, Alexander V. Slita, Anastasia V. Galochkina, Galina L. Starova, Andrey V. Ivanov, Alexander P. Molchanov

Research output

6 Citations (Scopus)

Abstract

The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.

Original languageEnglish
Pages (from-to)2327 - 2331
Number of pages5
JournalTetrahedron Letters
Volume59
Issue number24
DOIs
Publication statusPublished - 2018

Fingerprint

Cycloaddition
Cycloaddition Reaction
Hydrogen Bonding
Human Influenza
Hydrogen bonds
nitrones
In Vitro Techniques

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{a40320ea7798452c8915dcb30beb3173,
title = "Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates",
abstract = "The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.",
keywords = "Cycloaddition, Indoles, Isoxazolidines, Nitrones",
author = "Dmitriev, {Viktor A.} and Efremova, {Mariia M.} and Novikov, {Alexander S.} and Zarubaev, {Vladimir V.} and Slita, {Alexander V.} and Galochkina, {Anastasia V.} and Starova, {Galina L.} and Ivanov, {Andrey V.} and Molchanov, {Alexander P.}",
year = "2018",
doi = "10.1016/j.tetlet.2018.04.066",
language = "English",
volume = "59",
pages = "2327 -- 2331",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "24",

}

Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates. / Dmitriev, Viktor A.; Efremova, Mariia M.; Novikov, Alexander S.; Zarubaev, Vladimir V.; Slita, Alexander V.; Galochkina, Anastasia V.; Starova, Galina L.; Ivanov, Andrey V.; Molchanov, Alexander P.

In: Tetrahedron Letters, Vol. 59, No. 24, 2018, p. 2327 - 2331.

Research output

TY - JOUR

T1 - Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates

AU - Dmitriev, Viktor A.

AU - Efremova, Mariia M.

AU - Novikov, Alexander S.

AU - Zarubaev, Vladimir V.

AU - Slita, Alexander V.

AU - Galochkina, Anastasia V.

AU - Starova, Galina L.

AU - Ivanov, Andrey V.

AU - Molchanov, Alexander P.

PY - 2018

Y1 - 2018

N2 - The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.

AB - The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C–H⋯O) and moderate (N–H⋯N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities.

KW - Cycloaddition

KW - Indoles

KW - Isoxazolidines

KW - Nitrones

UR - http://www.scopus.com/inward/record.url?scp=85047061589&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.04.066

DO - 10.1016/j.tetlet.2018.04.066

M3 - Article

VL - 59

SP - 2327

EP - 2331

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -